AN EFFICIENT PROCEDURE FOR THE DEMETHYLATION OF ARYL-METHYL ETHERS IN OPTICALLY PURE UNUSUAL AMINO-ACIDS

被引：22

作者：

LI, GG ^{[1
]}

PATEL, D ^{[1
]}

HRUBY, VJ ^{[1
]}

机构：

[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(00)73917-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient procedure was developed for the removal of methyl groups from aryl methyl ethers, without racemization, in derivatives of unusual amino acids that are of significant importance in the design of highly selective peptide and protein ligands with specific conformational and topographical features. Demethylation of aromatic amino acids can result in an appreciable increase in receptor affinity, hence the new mild procedure which have been developed represents a facile and practical method for demethylation of Tyr (OMe) derivatives, including novel sidechain ring or C-3 modified analogs.

引用

收藏

页码：5393 / 5396

页数：4

相关论文

共 11 条

[1]

AIHARA K, 1988, CHEM PHARM BULL, V36, P837

[2] THE SYNTHESIS OF THYROXINE AND RELATED SUBSTANCES .5. A SYNTHESIS OF L-THYROXINE FROM L-TYROSINE [J].

CHALMERS, JR ;

DICKSON, GT ;

ELKS, J ;

HEMS, BA .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (DEC) :3424-3433

[3] HOST GUEST COMPLEXATION .42. PREORGANIZATION STRONGLY ENHANCES THE TENDENCY OF HEMISPHERANDS TO FORM HEMISPHERAPLEXES [J].

DOXSEE, KM ;

FEIGEL, M ;

STEWART, KD ;

CANARY, JW ;

KNOBLER, CB ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (10) :3098-3107

[4]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P14

[5] COUNTERATTACK REAGENTS SODIUM TRIMETHYLSILANETHIOLATE AND HEXAMETHYLDISILATHIANE IN THE BIS-O-DEMETHYLATION OF ARYL METHYL ETHERS [J].

HWU, JR ;

TSAY, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) :5987-5991

[6]

LI G, 1993, IN PRESS PEPTIDES

[7] ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - AN ENANTIOSELECTIVE SYNTHESIS OF THE 4 ISOMERS OF D-O-METHYL-2',BETA-DIMETHYLTROSINE AND L-O-METHYL-2',BETA-DIMETHYLTYROSINE [J].

LI, GG ;

RUSSELL, KC ;

JAROSINSKI, MA ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1993, 34 (16) :2565-2568

[8] DIASTEREOSPECIFIC TANDEM MICHAEL-LIKE ADDITION ELECTROPHILIC BROMINATION - A ONE-POT TANDEM ASYMMETRIC-SYNTHESIS OF PRECURSORS OF UNUSUAL AMINO-ACIDS [J].

LI, GG ;

JAROSINSKI, MA ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1993, 34 (16) :2561-2564

[9] ASYMMETRIC-SYNTHESIS OF UNUSUAL AMINO-ACIDS - SYNTHESIS OF OPTICALLY PURE ISOMERS OF BETA-METHYLTYROSINE [J].

NICOLAS, E ;

DHARANIPRAGADA, R ;

TOTH, G ;

HRUBY, VJ .

TETRAHEDRON LETTERS, 1989, 30 (49) :6845-6848

[10] DEMETHYLATION OF ALIPHATIC METHYL ETHERS WITH A THIOL AND BORON-TRIFLUORIDE [J].

NODE, M ;

HORI, H ;

FUJITA, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2237-2240